Boron tribromide → (4-Hydroxy-3-methylphenyl)acetic acid

HRID 2119476Notes

Reaction equation

HRID 2119476 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:10][C:11]([OH:13])=[O:12])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1382764-Methoxy-3-methylphenylacetic acid

Product 1

HCID 23440817(4-Hydroxy-3-methylphenyl)acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-methoxyphenylacetic acid (2.3 g., 12.8 mmol) in anh CH2Cl2, cooled to 0° C., was added 15 ml of a solution of BBr3 (1.0 M in CH2Cl2) via syringe. After addition was complete, the reaction was allowed to warm to room temperature and then quenched with 5 ml water. The CH2Cl2 was removed and the residue was extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to yield the title compound (1.58 g, 75% yield): ES−MS (m/z) 167 [M+H]+.

Workup

  1. additionAfter addition
  2. customquenched with 5 ml water
  3. customThe CH2Cl2 was removed
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-24b59ef2bf6b4709a8f63c6630af3a16
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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